WHAT IS WORTH DOING, EVEN IF YOU THINK YOU MIGHT FAIL?
Risk, Purpose, and the Quiet Power of Courage
Failure isn’t the opposite of success—it’s often the path to it. For individuals in Maryland and DC, this reflection explores how meaningful risk-taking stretches our emotional capacity, deepens our purpose, and invites us to live more fully.
We all set goals for ourselves. Writing this blog is one of my goals. Collecting 52 blogs into a journal book was another one of my goals, which I have now completed. Another is finishing a book about raising boys with access to the full range of their feelings. Every hour that I spend with a client has a goal at the outset: to listen and guide the client to learn more about themselves and, in so doing, build understanding that leads to skills that will translate into beneficial action. These goals have been chosen with an eye to my expertise, leading me to expect success. The question above is very different.
If I expect failure, will I do it anyway? Will I risk failure? Reflecting on that is truly sobering.
Most of us take risks that I call safe.
When we truly risk failure, what drives the process?
Contemplating that question requires a deep dive into my psyche. Who am I? How can I discern a serious risk? Oh, of course, there are things I would never attempt, like walking a tightrope between the Twin Towers. The man who did that has an entirely different makeup from me. But what is my equivalent challenge?
Let’s examine the elements of such a challenge. First, it has to be within the range of my physical capability. If I am in a wheelchair, I am not doing the tightrope.
Second, it has to stretch my abilities to the limit. Philippe Petit, a tightrope walker, had the skill set to attempt a walk between the Twin Towers. He also had the experience of studying the elements of such a feat and planning carefully. Third, I must have a motive for placing this challenge before me. I need a reason to sustain the planning and motivation. So, taking on a challenge is serious business. Fourth, I have to be willing to risk failure, which can sometimes mean risking death.
Amelia Earhart comes to mind immediately. She was a financially comfortable woman, committed to a relationship, successful professionally, and well-known as a supporter of women’s causes. Her life looks fulfilling and influential. Yet, she takes on the challenge of a solo flight around the world. Being the first woman to accomplish this was her big enough “why” and she had the skill set. The task certainly challenged her to the limit. Despite her failure, she is admired for her attempt. She is a model for other women to take risks and set challenging goals.
What is worth doing, even if you think you might fail?
Want to explore how risk-taking fuels emotional growth and resilience? Visit UW Medicine’s guide to learning from failure, A Conscious Rethink’s reflections on risk and regret, and BetterUp’s strategies for taking risks that pay off.
If you’re reflecting on courage, purpose, or emotional growth, therapy can help. Learn more about individual therapy in Maryland and DC or explore therapeutic approaches that support insight, healing, and bold living.



